Worth It
by Jinny the Kisaragi
Summary: Castiel's on a mission, one that will redeem everything that has happened to the Winchesters over the past nine years. Rated T for swearing.
1. Chapter 1

Dean really didn't think about where he was going until he was there.

One minute, he was talking to his little brother, recalling the moments of their childhood when Sam's innocence hadn't been brutally snatched from him, all the while trying and failing to reign in his broken sobs and tears, shoulders shaking with each one that escaped, as he stood over Sam's lax form. The next, he was standing in the middle of the crossroads. The one person in his life that he swore to protect, who mattered more than anyone else, who he would gladly give up everyone he ever saved just to have one more moment with, who he couldn't go on without, was behind the locked doors of death, and the small wooden box Dean held in his hands was the key.

Well, that combined with his eternal soul.

_What else can I do?_

Green eyes filled with tears that spilled down ashen cheeks once more, and Dean felt his gut twist and a wave of nausea pass over him at the thought of living his life without the one person who had been his reason to get up in the morning since he was four years old. There would be no too big little brother riding shotgun while pretending to be annoyed by his music, no lectures about how burgers and pie were going to kill him one day, no one there to shoot him bitchfaces whenever he cracked a stupid joke or puppy dog eyes that could make Dean do just about anything, no prank wars, no having someone who could understand how he was feeling with just one look and know how to make it better even if they didn't know they were, no little brother, best friend, hunting partner, _everything_ all wrapped up into one overgrown puppy, _no one to bring him to that light at the end of the tunnel, no reason for living__–_

_No. _Ten more years with Sam in exchange for his tainted soul was a steal.

"Dean."

Adrenaline spiked through him at the sudden greeting and Dean sprang upwards, his hunter's instincts making him grab his gun before he even knew what he was doing. The box was dropped on the ground in his panic before he could notice the presence of the newcomer.

"What the hell, man?" He spat, lowering his gun and glaring with red rimmed eyes, which he quickly wiped salty tears from. "Aren't you supposed to wait until I actually put the damn thing in the ground?" The gun was tucked back into his waistband and he stooped to pick up the small box.

The man before him cocked his head slightly, much like a bird's. It pissed Dean off.

"You believe that I am a crossroads demon." He finally stated after his brief inspection, his voice low and gravelly. He looked a bit put off. Maybe somewhat offended. Dean continued to glare, even when the man's crystal blue eyes didn't flick to red.

"Well, _yeah_. Come on, I don't got all day." _I don't know how much longer I can go feeling this weight on my chest._

The dark haired man seemed to settle a little, his piercing blue eyes becoming just a slight softer. "I assure you, I am not a demon." He stated. "My name is Castiel. I am an Angel of the Lord. I would reassure that there is no need to fear me, but I'm certain that you do not, Dean Winchester."

A brief silence settled over them. The newcomer's trench coat billowed slightly in the breeze while Dean eyed him skeptically. Castiel could see his green eyes harden their stare and his jaw clench, fists squeezed tight until Dean was white knuckled.

"There's no such thing as angels." Dean stated with absolution, a dark undertone and a bite in his voice. "And if there were, I would kick their asses for not doing their damn jobs."

Castiel fought the urge to roll his eyes, continuing to stare intently at his friend (well, future friend). He was so _not _in the mood for this. He'd already had this conversation with Dean years ago, and received a knife in his vessel's torso for it (which Jimmy had most certainly _not _appreciated). Once was enough.

Another moment of intense staring and Castiel finally asked the question he'd been wondering for a very, very long time.

"And what exactly is our job, Dean?" Because that was the thing: every time he tried to do his job, Dean got it into his head that the angel was out to do him–or, Father help him, _Sam–_some form of harm. Yes, he'd made mistakes, but the only thing that he had ever tried to do is help them, like what he was _trying_ to do _now._ So _please, _tell him what, exactly, Dean thought he should be doing.

This earned him a hardened look from Dean, one that spoke annoyance and disgust and _I am so not ready to deal with your fucking shit right now because I've got a baby brother who's dead and needs saving and nothing is going to keep me from doing just that._

He'd gone a bit too far. Point taken. Castiel had somewhat forgotten what it had been like to have such sensitive human emotions.

"Alright, _Castiel._" The growl was so low it was almost a whisper. His face morphed from extremely pissed off to extremely pissed off _big brother _with something to prove. "Picture this: a baby, just six months old, lying in his crib completely defenceless, completely innocent, all cute and pudgy and giggly and all other applicable baby adjectives." He paused a moment, collecting his emotions and, Castiel mused, his temper. "A demon walks into his room, you with me? The demon proceeds to _feed him its blood._" Dean punctuated the words harshly and took a step closer to Castiel. "You'd, y'know, help him. Right?" The question was accompanied by Dean crossing his arms and shrugging seemingly casually. "And how about his mom dying and _burning_ on the ceiling above him? How about her? Cause, I mean, that's what I'd think angels would probably do. I could be wrong though."

Sarcasm, Castiel interpreted, a typical Winchester strategy for temporary concealment of violent outbursts. Of course he would help the baby, _Sam_, his friend, his _family, _knowing then what he learned from the Winchesters later. But at the time, he had his orders; it was imperative that the future Boy King be fed Azazel's blood. "Dean, I–"

"Then, the baby grows up, all hopeful and puppy dog eyed in this broken family," Dean continued, the corner of his lip quirking up the tiniest bit, "praying to angels every damn day for at least a little bit of hope in his messed up, crappy life…"

The elder Winchester grew silent a moment, and Castiel knew this was going to get bad _fast._

"Every day… every day for 23 fucking years, he prayed for a better life for his family, for himself, for… for…" he trailed off, clearing his throat because he did not trust himself to talk right now without his voice cracking. Mask firmly back in place, he continued, voice gravelly. "They were supposed to help him. They were supposed to keep him safe from demons and monsters and a life that he hated and now?" Dean paused with unshed tears glistening in his eyes, looking intently at Castiel and cataloguing the angel's somewhat ashamed expression. "He's _dead _because of it. My kid brother is dead because of something that was out of his control since he was six months old." _I was supposed to keep him safe from all those things too._ "So _yeah,_ if I ever come across an angel, I will pluck its feathers out and make it _eat them_."

Now _this _was familiar, Castiel thought. He knew how to deal with an angry, protective, threatening Dean.

"Dean." The angel treaded cautiously at first, gauging Dean's reaction. When Dean just continued to breathe sharply and heavily, he continued. "Sam Winchester's prayers have been answered. I am here to save you both, but you must do as I say." Dean scoffed, unshed tears glistening in his green eyes, but he pressed on. "I know that you are more than willing to sell your soul for your brother, that you care about him more than anything in the world, including yourself. And, as unhealthy a quality as it is, I have always admired that in you. Both of you." He mentally winced at his choice of tenses. Seeing as this was a past Dean, he wouldn't know about all their experiences together. "You're both unique, and so is the bond that holds strong between you. It's rare and special." And, to the untrained eye, old, very old. Many of the Heavenly Host had thought it possible that their Father had created this bond especially to beat the Devil, bestowing it only upon the two brothers who were worthy of such a gift and burden. But after spending years with the Winchesters, Castiel realized that it was made of nothing more than unconditional love, friendship, and brotherhood, grown strong from being forged and reforged in the hottest flames that Hell had to throw at it. The more it endured, the stronger it became.

Dean stayed silent, his gaze bore a hole into Castiel's head, and the angel took the lack of a rebuttal as a sign to continue.

"But this demon isn't going to give you ten years. It's going to give you just one."


	2. Chapter 2

**A/N: The only reason this next chapter is up so quickly is because I already had it written and I'm impatient. Enjoy!**

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><p><em>Previously...<em>

_"But this demon isn't going to give you ten years. It's going to give you just one."_

The hunter frowned. "Crossroads demons give the same deal to everyone, and I know for a fact that they stick to their contracts."

"_Please, _just listen to me." Castiel implored. getting a little exasperated. He forgot how stubborn Dean could be. "You're only causing yourself and Sam more pain and suffering by doing this."

A humourless chuckle from Dean. "Yeah? Cause I don't really see how I could suffer any more than I am at this point." He sneered, voice threatening to betray him and crack. "Also, how the fuck do you know all this? Do angels know everything past, present, and future or something?"

"I can use the power of my Grace to travel through time, Dean." Castiel deadpanned. "And I've used a significant amount and the help of a spell to travel almost nine years back to complete this mission."

"Wow, you take procrastination to a whole new level, don't you?"

"On the contrary, the concept of procrastination is meaningless if one has the ability to travel through time."

"If you're not here to save Sam like you said, fuck off."

"You only get one year, Dean!" Castiel raised his voice, and Dean could swear the ground started to rumble just slightly. "One year in which Sam is going to work himself day and night trying to get you out of this deal, one year that you spend in paralyzing fear of what awaits you at the end. And when the end comes, Sam will feel much like you do now. He will blame _himself!_" The angel paused for a moment to stare intently at Dean, continuing more softly, and the Earth stood still once more. "He will blame himself for not killing Jake Talley when he had the chance, for not working himself hard enough to find a way to break your contract, for letting you die and not being able to repay you for all you did for him."

Dean's jaw clenched. "He doesn't have to repay me for a damn thing."

Castiel cocked his head again, and those piercing blue orbs that seemed to inspect his very soul were seriously starting to piss Dean off. "How did you feel?" He murmured.

"Excuse me?"

"When your father sold his soul for you?"

The mention of his father took Dean aback, suddenly making his temper flare up even more. Green eyes hardened and bore back into blue ones, but Dean said nothing, only pulling his lips back into a soundless snarl.

"Dean, I can guarantee you that those feelings of loss, of grief, of utter _desperation _will transform Sam into a person that you won't like." He paused, "He will become an empty shell of the person he once was. Both of you battle constant pain, constant suffering. It's all one battle after another, sometimes against _each other._"

_Well then. _Dean could help staring dumbly for a moment. "Well yeah, I mean, I'll be in Hell. Of course it'll be hor–"

Dean froze. Against each other?

But how the fuck could they fight each other if Dean was in _Hell? _

The green eyed man felt his blood run cold. _No no no, is my deal all for nothing? Does Sammy get sent to Hell too? _But then again, if Sam got cast down the Pit as well, Dean was pretty fucking sure that he wouldn't be fighting with him. More like being _tortured_ with him.

Castiel said nothing, wanting to tell Dean every detail of what goes wrong but unable to reveal too much.

Apparently the silence was enough for the cogs to whirr in Dean's brain, and Castiel was suddenly glad Sam was able to formulate a backup plan.

"Are you saying that I _get out _of Hell?!" He questioned, cautiously joyous before barking out a laugh. "Oh, man! I mean, I always knew I was a badass, but _that…" _Castiel remained quiet, and Dean trailed off, wondering why.

"I'm not supposed to know that, am I?" He huffed another laugh. "It gonna mess up some kind of… I don't fuckin' know, some kind of time thing?"

"In your limited vernacular, yes, I suppose it would 'mess up some kind of time thing', had I not taken the proper precautions beforehand." Castiel reassured, albeit with a weary sigh. "If I cannot sway your decision and all that I have seen comes true, you will have no recollection of this conversation or of me." Though now that Dean knew he got out of Hell, it was going to make convincing him not to take the deal a whole lot harder.

Dean crossed his arms. "Well ain't that convenient. So, what, you're… Ghost of Christmas Yet to Come or some shit?"

Now it was Castiel's turn to stare. "I apologize, but I don't believe my vessel resembles the Grim Reaper in any way. Mortal eyes should be able to perceive this form. Perhaps you are ill?"

"What?" Dean scrunched his nose and blinked. "No, I just meant… look, are you just here to tell me the future for the shits and giggles or what? 'Cause from where I stand, saving Sam and getting out of my Hell deal seems like a pretty sweetass deal to me."

The angel stayed silent a moment, lips moving but nothing coming out. How would he even begin to describe the downward spiral that had become the lives of the Winchesters? He could go on for years about their suffering, forever burdened with the weight of the world on their shoulders. He could tell him about all the death, all the destruction, the loss, the heartbreak, about how it just wasn't _fair_ and they deserved all the good things in the world, how he would give it all to both brothers if he could, and something that felt like a very human emotion twisted within his chest at the thought of how much of that suffering had been because of him and his kind.

Castiel was a celestial being. He did not cry. But right now, he thought he might.

"Dean," he started softly and slowly, "you would not be able to fathom the monstrosities that the world has for you and your brother, should you decide to make this deal." The words were almost whispered, and it was the most solemn thing Dean had heard Castiel say this whole time. It didn't scare him, because Dean Winchester _does not_ get scared, but it did send a bit of a chill down his spine. What the hell had this guy seen?

Dean clenched and unclenched his jaw, pupils darting to the ground, searching for something to focus on besides the thought of Sam with a future worse than his already horrible past. He couldn't bear putting Sam through that. He dragged his little brother back into the life once, he wasn't about to do it again.

But another thing Dean couldn't bear was going through life without Sam.

What could he do? Maybe there was something this guy could do?

His breath caught in his throat as an idea leapt into his head.

"Save him." Dean croaked, still looking at the ground, but flicking his eyes up to meet the angel's after a moment.

"I beg your pardon." Castiel squinted a bit. "I've already informed you that's why I'm h–"

"No!" Dean snapped, "Save him! Heal him! You're an angel, right? Isn't that what you do? Perform miracles and shit?!"

The twisting feeling was back in the raven haired angel's chest. "I'm…" He sighed. "Would that I could. But as my current situation stands, I cannot."

"What the hell does that mean?!" Dean shouted, clenching his fists and leaning toward the angel. "Your 'current situation'? Oh, so, what, it's not a convenient time or something?" His anger began to bubble over. How _dare _this motherfucker come in here and pretend like he can save Sam, only to turn around and say it's all up to him? Not that Dean minded it being up to him in the first place. He was a big brother for a reason, after all, and it was a job he took very seriously.

"I cannot." Castiel repeated lowly, almost to himself. Dean had to strain his ears to hear. Castiel's hand now hovered around his throat as he shifted his eyes to the ground in what looked to be shame. "My Grace. I would give the last of it gladly to save Sam, to give you the life you both deserve, but as it stands, what little I have left will not be enough."

Dean frowned. This guy kept mentioning Grace, but what the hell was that? Wasn't that more of a quality than anything? "So you're telling me the only way I can save Sam from this apparently unfathomable future is to _not _save him?" He laughed bitterly, pacing a bit and putting his hands on his hips. "Ain't that a bitch." Dean's voice cracked and his lip quivered before fresh tears pooled in his haunted eyes. He turned away from Castiel, washing his hand down his face as he looked up at the sky. It was dark and inky without a single star.

It was almost like a physical pain for Castiel, seeing is friend like this. He could tell that Dean was barely hanging on by a thread, Sam being ripped away from his older brother as brutally as he was. The angel could remember observing it the first time it happened.

He remembered how horrible Dean's heartbroken wailing had sounded as he cradled his limp baby brother close to his chest and refused to let go. He remembered Dean burying his face into Sam's chocolate locks and shaking violently with sobs and cries as the reality of the situation had slammed into him like a brick wall. He remembered Dean snarling at Bobby and possessively clutching Sam impossibly closer when the old hunter had tried to suggest that they take Sam back to the Impala. He remembered Dean, gasping and choking on tears, lifting Sam's deadweight in his arms and trudging back and collapsing in the backseat of the Impala, refusing any help from Bobby. He remembered Bobby fishing the keys out of Dean's jacket pocket and starting up the vehicle as quick as he could while Dean sat in the back with Sam, the elder brother sitting with Sam's head in his lap and threading his fingers through Sam's silken hair, much like he did many times through their childhood. He remembered the stone faced expression Dean slipped into, shock and helplessness taking over. He remembered Dean laying Sam down onto a cold mattress as gently as humanly possible, as if Sam were made of china and might break if the wind blew too strongly. He remembered Dean practically radiating grief and sorrow as he downed every ounce of liquor he could.

And to Dean, even the Dean from his time period, this had all just happened yesterday.

Oh yeah, crying was very possible at this point for anyone, celestial being or not.


	3. Chapter 3

**What's this? I actually did things... a year later? Wow. Go me.**

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><p>Castiel knew he had to choose his words carefully.<p>

One wrong slip and Dean could be putting that box into the hole in the crossroads and that would be the end of it. He'd taken an accidental step in that direction already.

On the other hand, he couldn't take too many steps back either, because that would result in Dean giving up completely and ending his own life.

The angel took a deep breath before continuing. "It's… Dean, it's beyond words. You endure so much, so much suffering and anguish that no being should ever have to shoulder." His words held an almost motherly understanding. "You're betrayed, plotted against by virtually everything. Almost everyone you or Sam has ever loved is _dead_. And I… I don't want that for either of you." Castiel seemed sad, despairing, and Dean swallowed thickly, saying nothing and still staring up at the sky, almost as if he thought that his gaze could pierce the heavens and he'd be able to see whether or not Sam was okay.

"He's happy, Dean." The angel implored softly, voice thick with emotion. "You have it on good authority that he's in Heaven right now, and he'll be waiting there for as long as you need him to."

_As long as I need him to, _Dean thought, _meaning as long as it takes to eat a bullet._

"Dean," Castiel seemed chastising, "your brother would not want you to end your existence here on Earth simply because he's not with you for as long as you have left to endure."

Dean wondered if angels could somehow read minds. Considering all the crazy shit he'd seen in his life, it wasn't totally unbelievable.

"Is Sammy really that much better off…this way?" He whispered brokenly. He couldn't even bring himself to say 'dead'. Dean's thoughts began wandering to Sam lying cold and pale on the mattress, how stiff and _wrong _it looked for his little brother to be anything but alive and bubbling and eating salad and constantly asking questions and _Sammy no Sammy please _please _don't be dead I can't do this without you little brother I can't I can't I can't I don't _want_ to I won't–_

"I'm sorry, Dean." The Winchester, eyes bright with unshed tears, turned back to face Castiel, who looked genuinely sad and regretful. "I'm so, so sorry. But yes, it's for the best."

For a minute, Dean couldn't breathe. He didn't want Sam to be better off without him. He sure as hell wasn't better of without Sam, no matter what this 'Castiel' said. Come on, a future without Sam? What, was this guy _nuts_? How could that be the better choice? Even with all of this information of the future, Dean still couldn't believe that he and Sam could be miserable while they had this baby, the open road, and each other. For 23 years, Sam was all he had, and he was all Sam had, and that's the way he liked it.

Yeah, Sam left him for Stanford, which still stung a bit and the pain of those years alone still lingered, but despite the separation, Dean was still Sam's big brother. And being a big brother comes with rights and responsibilities.

_Responsibilities, Dean, responsibilities, _a little voice in his head chided, _you're responsible for giving Sam the best possible future he can have, and right now, the best choice is leaving him in heaven. Are you really going to be so selfish as to pull him back into this life again? Are you going to put the rights above the responsibilities?_

Dean winced. That was true, but… what about _him? _What was hegoing to do without _Sam_?

And besides, how did he know could he trust this guy? In his grief he hadn't even given a second thought if something had tried to attack him, but now… what if he was really a demon trying to sabotage him out of this, knowing that the Winchester boys were stronger together?

Dean definitely wasn't trying to convince himself that making the deal was the better choice here.

Because he had always and would always know what was best for Sam.

After all, who had taught Sam how to tie his shoelaces? How to drive a car? Read him bedtime stories when he was a kid? Fallen victim countless times to the kid's puppy dog eyes into giving him the last of the Lucky Charms? Took him out for ice cream when he brought home straight A's? Took him out for ice cream _anyway, _whether or not there was actually a legitimate reason? Helped him get his first date? Been there for him when Jessica died? Been there when he started getting visions? Been there _his entire life?_

_This guy right here._

So who was most entitled to the right of doing what was best for Sam?

_Damn straight it's me. _

And was he really going to trust this guy with Sam when he rarely even trusted his own father with the kid?

_Hell nah._

_And if my choices are a future without Sam or having to cope with a shitty one with my little brother, barely scraping by, there's no comparison._

And despite not knowing yet that he and Sam were to share a heaven, he couldn't help but _feel_ his big brother senses tingling.

_Sammy's scared._

_Sammy's lonely. _

_Sammy's sad._

Dean had been silent for a while, still facing away from Castiel and staring with shimmering eyes up into the sky. The angel really didn't mean to invade Dean's privacy and read his thoughts, but sometimes Dean just projected them so _loudly _that they couldn't _not _be heard.

And he definitely heard Dean's protective radar going off.

Castiel did not voice it, but he too had seen the look in Sam's eyes that screamed he was missing something, a last piece, and the place he was in wouldn't truly become Heaven until that missing piece was there. His mind wandered a moment in the silence, remembering the content but not quite fulfilled or at peace look that the younger Winchester sported as he took in his surroundings.

Heaven was wherever the soul wanted it to be. Castiel was sure that Sam had visited many other places in his short stay; the beach with Jessica, his mother, his father, but at that moment, the Winchester Heaven was Bobby Singer's house, and Sam was leafing through a book that had been his grade seven favourite, _Where the Red Fern Grows. _The young man looked to have no intentions of getting up. He sat on the couch with a blanket on his lap, sandwich on a plate, and the book in his hands. He was comfortable, and yet extremely not. Castiel could feel confusion and anxiety radiating off Sam like waves.

_Where's Dean?_

Castiel would have told Dean how uncomfortable Sam had felt, not knowing where his brother was, but it would have shattered all hope at getting Dean to change the course of the future.

Or maybe, the angel mused, it would have simply shattered _Dean_, and Castiel didn't have the heart to do that.

The angel couldn't hold it in. A ghost of a sad smile appeared on his face, his heart clenching painfully again for the two souls he viewed above all humanity, for the sacrifices they shouldn't have had to make, yet remaining impossibly pure and true and always with the best interests and intentions of the innocent at heart.

_The road to Hell is paved with good intentions, _a traitorous voice in Castiel's head sneered, and the smile disappeared.

The angel looked up to see a cascade of emotions running across Dean's face. Grief, anguish, helplessness… contemplation?

Surely he couldn't be… _considering _putting himself and Sam through all he had just shared?

Oh no, Dean...

"I know you may think that you'll be able to handle it," Castiel spoke up quickly, wanting to put an end to Dean's indecision, "but let me tell you that, in my time, neither you or Sam have been carefree whatsoever for a very, very long time."

Dean shook his head slowly. "I don't believe you." He growled, jaw set.

"You Winchesters…" The soldier of heaven sighed, his lips quirking up into a wobbly smile as he closed his eyes briefly and remembered Sam's soul radiating pure need to be with his brother/best friend/life long constant/only source of comfort. _…no matter what the consequence or cost, you two always seem to choose each other._

The hunter was silent for a long time, and Castiel wondered if he had just succeeded in his task.

"But… me and Sam, we're fighting this thing _together?"_

His eyes flicked up to meet Castiel's.

"Worth it."

He dropped the box into the hole, and Castiel vanished.


End file.
